Sodium Bisulfate → HCID 67440685, compound

HRID 1483719Notes

Reaction equation

C([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[B:28]1[O:32]C(C)(C)[C:30](C)(C)[O:29]1)[O:6][C:7]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[C:10]([C:11]#[N:12])=[CH:9][N:8]=1)=O.[BH4-].[Na+].OS([O-])(=O)=O.[Na+]>CO>[OH:32][B:28]1[C:27]2[CH:26]=[CH:25][C:5]([O:6][C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][O:20]4)[C:10]([C:11]#[N:12])=[CH:9][N:8]=3)=[CH:4][C:3]=2[CH2:30][O:29]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-nicotinonitrile (0.5 g, 1.02 mmol) in methanol (3 mL) at 0° C. was added sodium borohydride (0.07 g, 2.04 mmol). After 1 h at room temperature, the solution was cooled in an ice bath and 1M NaHSO4 (2.6 mL, 2.6 mmol) was added until pH reached to 4-5. The resulting mixture was sonicated and stirred at 0° C. for 1 h. The white solid that separated was filtered, washed with MeOH and lyophilized to yield the title compound D118 (0.1 g, 25%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (s, 1H), 8.46 (s, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 7.15-7.09 (m, 1H), 7.02 (s, 1H), 4.99 (s, 2H), 4.71 (s, 1H), 4.49-4.40 (m, 2H), 4.02-3.91 (m, 1H), 3.84-3.73 (m, 2H), 3.49-3.41 (m, 1H), 1.72-1.58 (m, 2H), 1.55-1.41 (m, 4H); MS (ES) m/z: 397 (M+1)+; HPLC purity 97.55% (Maxplot), 97.65% (220 nm).

Workup

temperaturethe solution was cooled in an ice bath
customThe resulting mixture was sonicated
customThe white solid that separated
filtrationwas filtered
washwashed with MeOH

Sources & evidence

ORD record: ord-0548da6e50e4476ba188a6a81c598dae
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416146B2

Reaction notes

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